You can take a single trip policy or an annual one for multiple trips up to 45 days duration and can

We are middle aged full time/permanent travellers living on a low budget. We travel by RV/Motorhome, backpacking and cruising staying in hostels, hotels, cruises caribbean house-sitting and more and can give you tips, help and advice to do the same.
Luckily we came across All Clear Travel who offer travel insurance for all medical conditions, for all ages and to all countries. We bought 12 nights for a cruise to Iceland, Faeroe Islands and Norway at a cost of 160 to cover Steve for medical and cancellation. For another cruises caribbean 10 we could have included baggage but have very little of value and this would be covered under my own annual policy.
You can take a single trip policy or an annual one for multiple trips up to 45 days duration and can tailor make both to cover the countries you intend visiting. Once you have keyed in your details they produce a list of the different companies that will offer you cover with prices and values cruises caribbean for cancellation etc.
Also on offer is a special cruise policy that also covers you for missed trips if you are ill and also compensates if you have to stay in your cabin for any reason or if the cruise ship fails to dock at a particular port and you miss a visit.